Polymer-supported O-alkylisoureas:: Useful reagents for the O-alkylation of carboxylic acids

被引:39
作者
Crosignani, S
White, PD
Linclau, B [1 ]
机构
[1] Univ Southampton, Sch Chem, Combinatorial Ctr Excellence, Southampton SO17 1BJ, Hants, England
[2] Merck Biosci Ltd, Novabiochem, Beeston NG9 2JR, England
关键词
D O I
10.1021/jo049239e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Polymer-supported O-alkylisoureas were prepared by reaction of an alcohol with a polymer-supported carbodiimide under copper(II) catalysis. These reagents were used to transform carboxylic acids into the corresponding methyl, benzyl, allyl, and p-nitrobenzyl esters in a highly chemoselective manner in high yields and in very high purity after simple resin filtration and solvent evaporation. The reactions could be carried out using both conventional or microwave heating, with reaction times as short as 3-5 min in the latter case, without compromising yield, purity, or chemoselectivity. Unfortunately, the corresponding solid-supported tert-butyl isoureas could not be prepared.
引用
收藏
页码:5897 / 5905
页数:9
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